"Whenever you're sitting across from some important person, always picture him sitting there in a suit of long red underwear. That's the way I always operated in business"
About this Quote
The intent is tactical. Kennedy is describing a negotiator’s hack for asymmetry: if the other person’s title, money, or proximity to power makes you tense, you’ll bargain badly. The underwear trick breaks the spell quickly, returning the encounter to what it actually is: two people trying to get something. It’s also a quiet confession of how he “operated in business” - not as a romantic believer in institutions, but as someone who read rooms, sized up egos, and treated prestige as leverage to be neutralized.
Context sharpens the cynicism. Joseph P. Kennedy rose in a world where access and reputation were currencies, from finance to Hollywood to diplomacy. In that ecosystem, the “important person” is often a performer with better costuming and stronger lighting. The humor is doing real work: it’s a psychological equalizer, but also a moral tell. If you can picture leaders in clownish underwear, you’re less likely to be cowed - and also less likely to be enchanted by their claims to virtue. This is realpolitik in a locker-room key: a reminder that the people steering history are still, unavoidably, human.
Quote Details
| Topic | Business |
|---|---|
| Source | Help us find the source |
| Cite |
Citation Formats
APA Style (7th ed.)
Kennedy, Joseph P. (2026, January 18). Whenever you're sitting across from some important person, always picture him sitting there in a suit of long red underwear. That's the way I always operated in business. FixQuotes. https://fixquotes.com/quotes/whenever-youre-sitting-across-from-some-important-5974/
Chicago Style
Kennedy, Joseph P. "Whenever you're sitting across from some important person, always picture him sitting there in a suit of long red underwear. That's the way I always operated in business." FixQuotes. January 18, 2026. https://fixquotes.com/quotes/whenever-youre-sitting-across-from-some-important-5974/.
MLA Style (9th ed.)
"Whenever you're sitting across from some important person, always picture him sitting there in a suit of long red underwear. That's the way I always operated in business." FixQuotes, 18 Jan. 2026, https://fixquotes.com/quotes/whenever-youre-sitting-across-from-some-important-5974/. Accessed 12 Feb. 2026.




